# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May  4 10:16:47 2020
#   Inital geometry file: a 143 line input string
#   Ligand name: (2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)[C@@H](OC(=O)/C=C/c2ccc(O)c(O)c2)C(O)=O
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 GKP  GKP  '(2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid'  ligand  50  34  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_GKP
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 GKP  C1   C  CR16   0  -0.325  -4.8350   2.0047   0.6004
 GKP  C10  C  CH1    0  -0.122  -0.6347  -2.9540  -0.4254
 GKP  C11  C  C      0   0.406  -0.2249  -2.9482  -1.9185
 GKP  C12  C  CH1    0  -0.123   0.5700  -2.9483   0.4913
 GKP  C14  C  C1     0  -0.447   3.2879  -0.5527   0.1215
 GKP  C15  C  C1     0  -0.220   4.5832  -0.3397   0.3837
 GKP  C16  C  C      0   0.141   5.3587   0.8440   0.0410
 GKP  C17  C  C1     0  -0.400   6.6967   0.9024   0.4457
 GKP  C18  C  C      0   0.309   7.4949   1.9927   0.1499
 GKP  C19  C  C      0   0.257   6.9509   3.0618  -0.5749
 GKP  C2   C  CR16   0  -0.356  -5.6085   3.1251   0.8514
 GKP  C20  C  C1     0  -0.351   5.6245   3.0105  -0.9837
 GKP  C21  C  C1     0  -0.326   4.8337   1.9163  -0.6812
 GKP  C22  C  C      0   0.407   0.1642  -2.8780   1.9839
 GKP  C3   C  CR6    0   0.282  -6.9015   3.2284   0.3532
 GKP  C4   C  CR6    0   0.306  -7.4277   2.1772  -0.4123
 GKP  C5   C  CR16   0  -0.438  -6.6489   1.0607  -0.6552
 GKP  C6   C  CR6    0   0.139  -5.3431   0.9532  -0.1605
 GKP  C7   C  C1     0  -0.219  -4.5866  -0.2535  -0.4598
 GKP  C8   C  C1     0  -0.447  -3.3063  -0.4944  -0.1511
 GKP  C9   C  C      0   0.610  -2.6771  -1.7773  -0.4997
 GKP  O1   O  O      0  -0.473  -3.2360  -2.6976  -1.0552
 GKP  O10  O  O      0  -0.582   0.5764  -1.9189   2.6506
 GKP  O11  O  OH1    0  -0.627  -8.6875   2.3263  -0.8689
 GKP  O12  O  OH1    0  -0.618  -7.6977   4.2903   0.5635
 GKP  O2   O  O2     0  -0.473  -1.4191  -1.8124  -0.0894
 GKP  O3   O  O      0  -0.583  -0.6083  -2.0021  -2.6206
 GKP  O4   O  OC    -1  -0.612   0.4623  -3.9303  -2.2567
 GKP  O5   O  O2     0  -0.473   1.3757  -1.8352   0.1128
 GKP  O6   O  O      0  -0.472   3.1881  -2.7336   1.0758
 GKP  O7   O  OH1    0  -0.635   7.7781   4.0936  -0.8333
 GKP  O8   O  OH1    0  -0.633   8.7775   1.9985   0.5679
 GKP  O9   O  OC    -1  -0.613  -0.5487  -3.8280   2.3586
 GKP  H1   H  HCR6   0   0.258  -3.8354   1.9586   1.0116
 GKP  H2   H  HCH1   0   0.249  -1.1949  -3.8687  -0.2164
 GKP  H3   H  HCH1   0   0.249   1.1122  -3.8809   0.3169
 GKP  H4   H  H      0   0.270   2.6787   0.1832  -0.3894
 GKP  H5   H  H      0   0.263   5.1314  -1.1200   0.9031
 GKP  H6   H  H      0   0.268   7.1287   0.0784   1.0022
 GKP  H7   H  HCR6   0   0.279  -5.2018   3.9349   1.4464
 GKP  H8   H  H      0   0.281   5.2074   3.8383  -1.5451
 GKP  H9   H  H      0   0.259   3.8065   1.9068  -1.0202
 GKP  H10  H  HCR6   0   0.276  -7.0617   0.2489  -1.2453
 GKP  H11  H  H      0   0.263  -5.1346  -1.0263  -0.9908
 GKP  H12  H  H      0   0.270  -2.6955   0.2351   0.3669
 GKP  H13  H  HOH1   0   0.476  -8.9429   1.5589  -1.3926
 GKP  H14  H  HOH1   0   0.478  -7.2423   4.9455   1.1043
 GKP  H16  H  HOH1   0   0.486   7.3350   4.7690  -1.3594
 GKP  H17  H  HOH1   0   0.474   9.2372   2.7827   0.2462
 GKP  C13  C  C      0   0.610   2.6391  -1.8153   0.5077

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 GKP  O8   C18  single    1.349  0.020  1.349
 GKP  C18  C17  aromatic  1.383  0.020  1.383
 GKP  C18  C19  aromatic  1.402  0.020  1.402
 GKP  C17  C16  aromatic  1.399  0.020  1.399
 GKP  O10  C22  deloc     1.239  0.020  1.239
 GKP  O9   C22  deloc     1.246  0.020  1.246
 GKP  O7   C19  single    1.347  0.020  1.347
 GKP  C19  C20  aromatic  1.389  0.020  1.389
 GKP  C16  C15  single    1.456  0.020  1.456
 GKP  C16  C21  aromatic  1.395  0.020  1.395
 GKP  C15  C14  double    1.339  0.020  1.339
 GKP  C22  C12  single    1.548  0.020  1.548
 GKP  O6   C13  double    1.211  0.020  1.211
 GKP  C20  C21  aromatic  1.383  0.020  1.383
 GKP  C14  C13  single    1.471  0.020  1.471
 GKP  C13  O5   single    1.324  0.020  1.324
 GKP  C12  O5   single    1.425  0.020  1.425
 GKP  C12  C10  single    1.514  0.020  1.514
 GKP  C10  O2   single    1.425  0.020  1.425
 GKP  C10  C11  single    1.548  0.020  1.548
 GKP  O2   C9   single    1.324  0.020  1.324
 GKP  C2   C1   aromatic  1.384  0.020  1.384
 GKP  C2   C3   aromatic  1.390  0.020  1.390
 GKP  C1   C6   aromatic  1.394  0.020  1.394
 GKP  O12  C3   single    1.344  0.020  1.344
 GKP  C3   C4   aromatic  1.403  0.020  1.403
 GKP  C8   C9   single    1.471  0.020  1.471
 GKP  C8   C7   double    1.339  0.020  1.339
 GKP  C9   O1   double    1.212  0.020  1.212
 GKP  C6   C7   single    1.455  0.020  1.455
 GKP  C6   C5   aromatic  1.400  0.020  1.400
 GKP  C4   C5   aromatic  1.383  0.020  1.383
 GKP  C4   O11  single    1.348  0.020  1.348
 GKP  C11  O3   deloc     1.239  0.020  1.239
 GKP  C11  O4   deloc     1.245  0.020  1.245
 GKP  C1   H1   single    0.930  0.020  1.080
 GKP  C10  H2   single    0.970  0.020  1.090
 GKP  C12  H3   single    0.970  0.020  1.090
 GKP  C14  H4   single    0.930  0.020  1.080
 GKP  C15  H5   single    0.930  0.020  1.080
 GKP  C17  H6   single    0.930  0.020  1.080
 GKP  C2   H7   single    0.930  0.020  1.080
 GKP  C20  H8   single    0.930  0.020  1.080
 GKP  C21  H9   single    0.930  0.020  1.080
 GKP  C5   H10  single    0.930  0.020  1.080
 GKP  C7   H11  single    0.930  0.020  1.080
 GKP  C8   H12  single    0.930  0.020  1.080
 GKP  O11  H13  single    0.850  0.020  0.980
 GKP  O12  H14  single    0.850  0.020  0.980
 GKP  O7   H16  single    0.850  0.020  0.980
 GKP  O8   H17  single    0.850  0.020  0.980

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 GKP  H1   C1   C6   120.81  3.000
 GKP  H1   C1   C2   118.80  3.000
 GKP  C6   C1   C2   120.39  3.000
 GKP  H2   C10  O2   110.08  3.000
 GKP  H2   C10  C12  107.17  3.000
 GKP  O2   C10  C12  106.99  3.000
 GKP  H2   C10  C11  108.86  3.000
 GKP  O2   C10  C11  111.72  3.000
 GKP  C12  C10  C11  111.92  3.000
 GKP  O4   C11  O3   128.24  3.000
 GKP  O4   C11  C10  113.89  3.000
 GKP  O3   C11  C10  117.87  3.000
 GKP  H3   C12  O5   110.09  3.000
 GKP  H3   C12  C22  108.82  3.000
 GKP  O5   C12  C22  111.63  3.000
 GKP  H3   C12  C10  107.16  3.000
 GKP  O5   C12  C10  106.98  3.000
 GKP  C22  C12  C10  112.05  3.000
 GKP  H4   C14  C15  121.90  3.000
 GKP  H4   C14  C13  117.31  3.000
 GKP  C15  C14  C13  120.79  3.000
 GKP  H5   C15  C16  115.34  3.000
 GKP  H5   C15  C14  117.89  3.000
 GKP  C16  C15  C14  126.77  3.000
 GKP  C21  C16  C17  118.52  3.000
 GKP  C21  C16  C15  123.11  3.000
 GKP  C17  C16  C15  118.37  3.000
 GKP  H6   C17  C18  118.62  3.000
 GKP  H6   C17  C16  119.86  3.000
 GKP  C18  C17  C16  121.53  3.000
 GKP  O8   C18  C19  121.74  3.000
 GKP  C19  C18  C17  119.20  3.000
 GKP  O8   C18  C17  119.06  3.000
 GKP  O7   C19  C20  123.93  3.000
 GKP  C20  C19  C18  119.65  3.000
 GKP  O7   C19  C18  116.42  3.000
 GKP  H7   C2   C3   119.36  3.000
 GKP  H7   C2   C1   119.63  3.000
 GKP  C3   C2   C1   121.00  3.000
 GKP  H8   C20  C21  119.83  3.000
 GKP  H8   C20  C19  119.46  3.000
 GKP  C21  C20  C19  120.71  3.000
 GKP  H9   C21  C20  118.77  3.000
 GKP  H9   C21  C16  120.84  3.000
 GKP  C20  C21  C16  120.39  3.000
 GKP  O9   C22  O10  128.25  3.000
 GKP  O9   C22  C12  113.92  3.000
 GKP  O10  C22  C12  117.83  3.000
 GKP  O12  C3   C4   117.08  3.000
 GKP  C4   C3   C2   119.27  3.000
 GKP  O12  C3   C2   123.64  3.000
 GKP  O11  C4   C5   123.79  3.000
 GKP  O11  C4   C3   116.90  3.000
 GKP  C5   C4   C3   119.31  3.000
 GKP  H10  C5   C6   119.30  3.000
 GKP  H10  C5   C4   119.03  3.000
 GKP  C6   C5   C4   121.67  3.000
 GKP  C7   C6   C5   118.40  3.000
 GKP  C5   C6   C1   118.35  3.000
 GKP  C7   C6   C1   123.25  3.000
 GKP  H11  C7   C8   117.85  3.000
 GKP  H11  C7   C6   115.36  3.000
 GKP  C8   C7   C6   126.79  3.000
 GKP  H12  C8   C9   117.36  3.000
 GKP  H12  C8   C7   121.89  3.000
 GKP  C9   C8   C7   120.75  3.000
 GKP  O2   C9   O1   124.08  3.000
 GKP  O1   C9   C8   125.02  3.000
 GKP  O2   C9   C8   110.87  3.000
 GKP  H13  O11  C4   110.10  3.000
 GKP  H14  O12  C3   110.18  3.000
 GKP  C9   O2   C10  118.11  3.000
 GKP  C13  O5   C12  118.17  3.000
 GKP  H16  O7   C19  111.03  3.000
 GKP  H17  O8   C18  110.69  3.000
 GKP  O6   C13  O5   124.12  3.000
 GKP  O5   C13  C14  110.82  3.000
 GKP  O6   C13  C14  125.02  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 GKP  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 GKP  CONST_02  C4   C5   C6   C1      0.00   0.0  0
 GKP  CONST_03  C19  C18  C17  C16     0.00   0.0  0
 GKP  CONST_04  C19  C20  C21  C16     0.00   0.0  0
 GKP  CONST_05  C20  C19  C18  C17     0.00   0.0  0
 GKP  CONST_06  C20  C21  C16  C17     0.00   0.0  0
 GKP  CONST_07  C21  C16  C17  C18     0.00   0.0  0
 GKP  CONST_08  C21  C20  C19  C18     0.00   0.0  0
 GKP  CONST_09  C5   C6   C1   C2      0.00   0.0  0
 GKP  CONST_10  C5   C4   C3   C2      0.00   0.0  0
 GKP  CONST_11  C6   C1   C2   C3      0.00   0.0  0
 GKP  CONST_12  C6   C5   C4   C3      0.00   0.0  0
 GKP  CONST_13  O12  C3   C2   C1    180.00   0.0  0
 GKP  CONST_14  C18  C17  C16  C15   180.00   0.0  0
 GKP  CONST_15  C20  C21  C16  C15   180.00   0.0  0
 GKP  CONST_16  O8   C18  C17  C16   180.00   0.0  0
 GKP  CONST_17  O7   C19  C18  C17   180.00   0.0  0
 GKP  CONST_18  C7   C6   C1   C2    180.00   0.0  0
 GKP  CONST_19  O11  C4   C3   C2    180.00   0.0  0
 GKP  CONST_20  O8   C18  C19  C20   180.00   0.0  0
 GKP  CONST_21  O7   C19  C20  C21   180.00   0.0  0
 GKP  CONST_22  C7   C6   C5   C4    180.00   0.0  0
 GKP  CONST_23  O12  C3   C4   C5    180.00   0.0  0
 GKP  CONST_24  O11  C4   C5   C6    180.00   0.0  0
 GKP  CONST_25  H10  C5   C6   C1    180.00   0.0  0
 GKP  CONST_26  H8   C20  C21  C16   180.00   0.0  0
 GKP  CONST_27  H9   C21  C16  C17   180.00   0.0  0
 GKP  CONST_28  H6   C17  C18  C19   180.00   0.0  0
 GKP  CONST_29  H1   C1   C2   C3    180.00   0.0  0
 GKP  CONST_30  H7   C2   C3   C4    180.00   0.0  0
 GKP  Var_01    C8   C7   C6   C1     -5.12  30.0  2
 GKP  Var_02    C17  C16  C15  C14   177.66  30.0  2
 GKP  Var_03    C16  C15  C14  C13   178.84   0.0  2
 GKP  Var_04    C9   C8   C7   C6    178.94   0.0  2
 GKP  Var_05    C8   C9   O2   C10  -175.93  30.0  3
 GKP  Var_06    O6   C13  O5   C12     6.43  30.0  1
 GKP  Var_07    O2   C9   C8   C7   -179.17  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 GKP  chir_01  C10  C12  O2   C11  negativ
 GKP  chir_02  C12  O5   C10  C22  positiv

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 GKP  plan-1  C15  0.020
 GKP  plan-1  C16  0.020
 GKP  plan-1  C17  0.020
 GKP  plan-1  C18  0.020
 GKP  plan-1  C19  0.020
 GKP  plan-1  C20  0.020
 GKP  plan-1  C21  0.020
 GKP  plan-1  O7   0.020
 GKP  plan-1  O8   0.020
 GKP  plan-1  H6   0.020
 GKP  plan-1  H8   0.020
 GKP  plan-1  H9   0.020
 GKP  plan-2  C1   0.020
 GKP  plan-2  C2   0.020
 GKP  plan-2  C3   0.020
 GKP  plan-2  C4   0.020
 GKP  plan-2  C5   0.020
 GKP  plan-2  C6   0.020
 GKP  plan-2  C7   0.020
 GKP  plan-2  O11  0.020
 GKP  plan-2  O12  0.020
 GKP  plan-2  H1   0.020
 GKP  plan-2  H7   0.020
 GKP  plan-2  H10  0.020
 GKP  plan-3  C10  0.020
 GKP  plan-3  C11  0.020
 GKP  plan-3  O3   0.020
 GKP  plan-3  O4   0.020
 GKP  plan-4  C12  0.020
 GKP  plan-4  C22  0.020
 GKP  plan-4  O10  0.020
 GKP  plan-4  O9   0.020
 GKP  plan-5  C14  0.020
 GKP  plan-5  C15  0.020
 GKP  plan-5  C16  0.020
 GKP  plan-5  H4   0.020
 GKP  plan-5  H5   0.020
 GKP  plan-5  C13  0.020
 GKP  plan-6  C14  0.020
 GKP  plan-6  O5   0.020
 GKP  plan-6  O6   0.020
 GKP  plan-6  C13  0.020
 GKP  plan-7  C6   0.020
 GKP  plan-7  C7   0.020
 GKP  plan-7  C8   0.020
 GKP  plan-7  C9   0.020
 GKP  plan-7  H11  0.020
 GKP  plan-7  H12  0.020
 GKP  plan-8  C8   0.020
 GKP  plan-8  C9   0.020
 GKP  plan-8  O1   0.020
 GKP  plan-8  O2   0.020

